And do I have the panache to do it wrong on purpose?

If my shirt has those little button dealies on the collar, meant to button them to the shirt body, are there any circumstances under which they should be unbuttoned? What if I am wearing a sweater over it and it looks stupid to have them buttoned? Am I wearing my shirts wrong? –Dan, Arlington, Va.

Troy Patterson

Photo by Christina Paige

Thank you for your question, Dan. I appreciate your distress, and I do not mean to belittle it in saying that I very much appreciate this opportunity to promote a cause: People tend to refer to those little button dealies as collar buttons, and I’d rather that we call them point buttons. Doing so would help to avoid confusion with both the neck button that you fasten when you put on a tie to go work (if you are the kind of guy who wears a tie to work) and with the mechanism by which you fix a detachable collar to your shirt to go to work (if you are the kind of guy who wears a chancery wig or a mitre or something to work).

The first thing you need to know is that conventional wisdom dictates that you always leave the house with your point buttons buttoned. The second thing you need to know is to disregard the first thing as often as your gut-level sensibilities allow. If the context accommodates this sartorial insouciance, then go for it. I leave my point buttons unbuttoned more often than not. Now, I wouldn’t dream of turning up at a funeral service looking like that—I believe in wearing a tie to a funeral, and I do not believe that I have what it takes to wear undone point buttons with a tie. But on more light-hearted occasions, those that require merely a jacket, such as a day at the races or a wake with an open bar, I give it some consideration.

An understanding of history may help you to appreciate my stance. The button-down collar dates to the 1890s, when John E. Brooks—a scion of the Brooks Brothers empire—took a trip to England and went, as scions will, to a polo match. Polo is, of course, a vigorous sport, what with all the galloping on the field and the gold-digging on the sidelines (cf. Dr. Thompson’s “Polo Is My Life,” RS 697); players had begun telling their valets to tell their tailors to do something to keep their deuced shirt collars from flopping about so bloody much. Brooks, admiring the result, bit their style, and launched a line of oxford-cloth button-down shirts. I offer this context to say that the garment, having begun its existence as sportswear, is best worn sportily; that the point buttons are in some sense vestigial organs; and that today Brooks Brothers makes a no-iron OCBD that will revolutionize your approach to not ironing.

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That’s my personal position, but it is in this matter paramount that you know thyself, bro.

If you feel that you look stupid buttoning down a button-down beneath a sweater, your carriage will reflect this felt stupidity, and you will, in consequence, look stupid, and your immediate vicinity will become a less attractive place, and you’ll be bringing every body else down. Therefore, I am strongly tempted to recommend that you leave the point buttons unbuttoned.

Caveat: Leaving the buttons unbuttoned might, in fact, result in a look that’s slightly more stupid than that of helplessly projecting meta-conscious awkwardness. Leaving the buttons unbuttoned requires a certain style of studied casualness that cannot be taught. You can only be confident of getting away with breaking from convention if you are instinctively confident of your ability to make the break, and the fact that you felt the need to ask the question might be an ill omen.

So: Yes, you may leave your point buttons unbuttoned. But can you? Here is one way of approaching a self-assessment: You are statistically more likely to carry this off successfully if the shirt in question is, for instance, preppy pink as opposed to IBM white. This has nothing to do with the color of the shirt but with the character of the shirt owner. The man who wears a pink shirt has already begun to demonstrate his potential for the requisite panache.

Gianni Agnelli with his father in 1940

Photo courtesy of DGT Media - Simone/Wikimedia Commons

To put it another way: Are you the kind of guy who can imagine himself owning an Alfa Romeo? What about owning Alfa Romeo? The unbuttoned-point-button look is known within the shirt-collar-caring-about community as the Agnelli, in reference to Gianni Agnelli (1921-2003), who once headed Fiat and will always head all-time best-dressed lists. That Agnelli could pull off wearing unbuttoned Brooks Brothers button-downs with double-breasted suits while wearing his wristwatch wrapped around his cuff is a testament to his hall-of-fame sprezzatura—his dashing mastery of an artful carelessness of style. It must have helped that Agnelli, as the richest man in Italy since the Medicis, felt entitled to express an abundance of menefreghismo. Unbuttoned point buttons were, for him, the collarly equivalent of the blaringly loud go-to-hell pants memorably described by Tom Wolfe as the tribal colors of the trad class. To gauge your ability to follow his example, you must first calculate how much of a damn you give about what the rest of us think.

In my reckoning, the foremost American exponent of the look is Philadelphia’s Robert Venturi, the architect who, with Denise Scott Brown, wrote Learning From Las Vegas and created buildings on many of the college campuses where styles of preppy insouciance are cultivated, preserved, and perfected. Here he is in 1991, in the portrait shot to commemorate his Pritzker Prize, wearing a rep tie and a smirk that rhymes with the attitude of his shirt collar. I would not be the first person to make a connection between his undone button-down and his postmodernist design philosophy, which privileges “messy vitality.” Sometimes it is good style for form to flout function.

Troy Patterson is Slate’s writer at large and a contributing writer at the New York Times Magazine.